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Issue 3, 2016
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Determination of enantiomeric excess of carboxylates by fluorescent macrocyclic sensors

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Abstract

Chiral fluorescent chemosensors featuring macrocycles comprising BINOL auxiliary and an array of hydrogen bond donors were synthesized. To enhance fluorescence of the chemosensors, conjugated moieties were attached to the 3,3′-positions of the BINOL auxiliary. The resulting chemosensors recognize a number of carboxylates, namely, enantiomers of ibuprofen, ketoprofen, 2-phenylpropanoate, mandelate, and phenylalanine in a stereoselective fashion. Depending on the structure of the chemosensor, the presence of carboxylate yields fluorescence quenching or amplification. This information-rich signal can be used to determine the identity of the analyte including the sense of chirality. Quantitative experiments were performed aimed at analysis of enantiomeric excess of chiral carboxylates. The quantitative analysis of enantiomeric composition of ibuprofen, ketoprofen, and phenylalanine shows that the sensors correctly identify mixtures with varying enantiomeric excess and correctly predict the enantiomeric excess of unknown samples with error of prediction <1.6%.

Graphical abstract: Determination of enantiomeric excess of carboxylates by fluorescent macrocyclic sensors

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Supplementary files

Article information


Submitted
06 Nov 2015
Accepted
09 Dec 2015
First published
14 Dec 2015

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2016,7, 2016-2022
Article type
Edge Article
Author version available

Determination of enantiomeric excess of carboxylates by fluorescent macrocyclic sensors

A. Akdeniz, T. Minami, S. Watanabe, M. Yokoyama, T. Ema and P. Anzenbacher, Chem. Sci., 2016, 7, 2016
DOI: 10.1039/C5SC04235F

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